Methyl iodide → HCID 67279277, compound

HRID 1943273Notes

Reaction equation

HRID 1943273 reaction equation
[H-].[Na+].[CH2:3]([N:5]([CH3:26])[C:6]([CH:8]1[CH2:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[C:15]([F:25])[CH:14]=2)([OH:12])[CH2:9]1)=[O:7])[CH3:4].[CH3:27]I>C1COCC1>[CH2:3]([N:5]([CH3:26])[C:6]([CH:8]1[CH2:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[C:15]([F:25])[CH:14]=2)([O:12][CH3:27])[CH2:9]1)=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 56648225HCID 56648225, compound2×

Product 1

HCID 67279277HCID 67279277, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% wt, 0.040 g, 1.00 mmol) was added to a solution of Example 14, 3-(3-Fluoro-4-pyrrolidin-1-ylmethyl-phenyl)-3-hydroxy-cyclobutanecarboxylic acid ethyl-methyl-amide (0.25 g, 0.748 mmol) in THF (5 mL). After stirring for 15 min, all gas evolution ceased and methyliodide (0.06 mL, 0.96 mmol) was added. The resulting mixture was stirred at room temperature for 16 h then quenched with water and extracted into EtOAc. The extract was washed with brine, dried over MgSO4 and concentrated to give the title compound as a light yellow oil (0.13 g): Rf=0.16 (20% MeOH/EtOAc); LRMS m/z Calcd for C20H29FN2O2, 348.5, found, 349.4 (M+H) APCI.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 16 h
  2. customthen quenched with water
  3. extractionextracted into EtOAc
  4. washThe extract was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2028cd5b89ac4527b808fb0a74d7da8e
Source dataset
uspto-grants-2013_03
Patent number
US08389743B2

Reaction notes

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